Ethyl Bromide → Ethyl alpha-Phenyl-alpha-phenylethynylglycolate

HRID 358242

반응식

HRID 358242 반응식
[C:1]1([C:7]#[CH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Mg]Br)C.[Mg].C(Br)C.C1(C#C[Mg]Br)C=CC=CC=1.[C:27]1([C:33](=[O:39])[C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CCOCC>[C:27]1([C:33]([C:8]#[C:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([OH:39])[C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

참가 물질

8

반응물 6

HCID 6332Ethyl BromideHCID 10821PhenylacetyleneHCID 15349Ethyl benzoylformateHCID 5462224MagnesiumHCID 178418443HCID 178418443, 화합물HCID 178419644HCID 178419644, 화합물

생성물 1

HCID 12328607Ethyl alpha-Phenyl-alpha-phenylethynylglycolate

시약·촉매·용매 1

HCID 3283Diethyl Ether용매3회

실험 절차

A solution of phenylacetylene (11.2 g., 0.1 mole) in 25 ml. of anhydrous ether was added over a 45 minute period to a suspension of ethylmagnesium bromide (0.1 mole) prepared from magnesium (2.4 g., 0.1 g. atom) and ethyl bromide (10.9 g., 0.1 mole) in 100 ml. of ether. The mixture was stirred overnight. The resultant phenylethynylmagnesium bromide suspension was subsequently added dropwise through a stop-cock at the base of the flask to a solution of ethyl phenylglyoxylate (17.8 g., 0.1 mole) in 100 ml. of dry ether at 0°-5° over a two hour period. The cooling bath was removed and the mixture stirred for five hours. The reaction mixture was kept overnight, then poured on a slurry of ice and concentrated hydrochloric acid and extracted with ether. The ether extracts were dried and the solvent distilled in vacuo. The resultant oil was distilled to give 14.5 g. (52%) of product, b.p. 170°-82° (0.25 mm.). An analytical sample distilled at 156°-58° (0.08 mm.).

후처리

  1. customThe cooling bath was removed
  2. stirringthe mixture stirred for five hours
  3. waitThe reaction mixture was kept overnight
  4. additionpoured on a slurry of ice and concentrated hydrochloric acid
  5. extractionextracted with ether
  6. dry with materialThe ether extracts were dried
  7. distillationthe solvent distilled in vacuo
  8. distillationThe resultant oil was distilled
  9. customto give 14.5 g
  10. distillationAn analytical sample distilled at 156°-58° (0.08 mm.)

출처 및 근거

ORD 기록
ord-eddc612bbc884e04842e80996f6a0f5b
출처 데이터셋
uspto-grants-1984_08
특허 번호
US04465834

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